76 PROCEEDINGS OP THE AMERICAN ACADEMY 



fore, is similar to the well known conversion of the so-called nitrotar- 

 taric acid into tartronic acid. 



Tho nitrite of bromtriuitrophenylmalonic ester is almost insoluble 

 in cold water, perhaps a little more soluble in boiling water ; but if the 

 substance was boiled for some time with water, the crystals were con- 

 verted superficially into a daik red oily substance, and the water gave 

 a slight test for bromine; this decomposition seemed to be due, how- 

 ever, only to the heat (see above), nut to the presence of tlie water. 

 It is slightly soluble in cold, more freely in liot ethyl alcohol, but this 

 solution is easily decomposed by heat, since boiling for fifteen minutes 

 converts the substance completely into a brownish red viscous product 

 resembling half-dried varnish, from which nothing definite could be 

 isolated, and even a very short heating with alcohol is sufficient to 

 form some of this viscous body. Its solubility in methyl alcohol 

 resembles that in ethyl alcohol; it is freely soluble in chloroform, or 

 acetone; soluble in benzol, or glacial acetic acid; slightly soluble in 

 carbonic disulphide ; very slightly in ether, and essentially insoluble in 

 ligroine. The best solvent for it is the mixture of chloroform and 

 alcohol described above. Strong sulphuric acid seems to have no 

 action on it in the cold, or if heated, until the substance decomposes, 

 when it dissolves forming a reddish solution ; strong hydiochloric acid 

 has no action on it, either hot or cold, as long as the substance does 

 not decompose ; strong nitric acid has little or no action on it in the 

 cold, even when allowed to stand with it for some weeks, when heated 

 to 100° it converts it gradually into the bromtrinitrojjhenyltartronic 

 ester, as is described in detail later in this paper under the preparation 

 of that substance. 



Ammoiiic hydrate acts on it little, if at all, even when the action 

 is assisted by the addition of alcohol ; sodic hydrate in aqueous so- 

 lution has no action, but if alcohol is added the crystals begin to dis- 

 solve slowly, imparting a red color to tlie liquid but only a partial 

 solution is effected m the cold. From this observation we inferred 

 that no salt was formed until the nitrite was decomposed, and to test 

 the accuracy of this inference we treated some of the nitrite with an 

 alcoholic solution of sodic etliylate, which gave at once a daik blood- 

 red coloration ; but even here ordy a part, and that not the larger part, 

 of the crystals of the nitrite was dissolved ; the red solution poured 

 off from the unaltered crystals gave a good test for a nitrite with 

 starch paste, potassic iodide, and dilute sulphuric acid, with ferrous 

 8ul[»hate and sidphuric acid, and by Liebermann's reaction, so that 

 there can be no doubt that sodic nitrite was formed in the experiment 



